Ammonium formate → HCID 10142908, compound

HRID 2300233Notes

Reaction equation

HRID 2300233 reaction equation
C([N:8]([CH:27]1[CH2:30][N:29]([S:31]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][CH2:43][CH3:44])=[CH:36][CH:35]=2)(=[O:33])=[O:32])[CH2:28]1)[CH2:9][CH:10]([OH:26])[CH2:11][O:12][C:13]1[C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]=2[CH:16]=[CH:15][CH:14]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH2:41]([O:40][C:37]1[CH:38]=[CH:39][C:34]([S:31]([N:29]2[CH2:28][CH:27]([NH:8][CH2:9][CH:10]([OH:26])[CH2:11][O:12][C:13]3[C:25]4[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[NH:18][C:17]=4[CH:16]=[CH:15][CH:14]=3)[CH2:30]2)(=[O:33])=[O:32])=[CH:35][CH:36]=1)[CH2:42][CH2:43][CH3:44]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 12044734HCID 12044734, compound

Product 1

HCID 10142908HCID 10142908, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-{Benzyl-[1-(4-butoxy-benzenesulfonyl)-azetidin-3-yl]-amino}-3-(9H-carbazol-4-yloxy)-propan-2-ol (0.18 g, 0.3 mmol) in methanol (6 ml) was added ammonium formate (0.29 g, 4.5 mmol), and 0.045 g of 10% Pd/C. The mixture was stirred at reflux for 18 h. After cooling to room temperature, it was filtered through Celite. The solvent was evaporated and the residue triturated with isopropyl ether to give 0.14 g of a white solid; m.p. 81-84° C.; MS (ES) m/z 524.0 (MH+); HRMS (ES) Calcd. for C28H34N3O5S (MH+): 524.2219, Found: 524.2252.

Workup

  1. temperatureat reflux for 18 h
  2. filtrationit was filtered through Celite
  3. customThe solvent was evaporated
  4. customthe residue triturated with isopropyl ether

Sources & evidence

ORD record
ord-8dbecb5a0ffe4f258e90593dd9214608
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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